L-epinephrine
Conditions | Yield |
---|---|
With ammonium hydroxide In water at 5 - 10℃; for 0.5h; pH=8.5; | 100% |
(R)-1-(3,4-Dimethoxy-phenyl)-2-methylamino-ethanol
L-epinephrine
Conditions | Yield |
---|---|
With boron tribromide | 97% |
L-epinephrine
Conditions | Yield |
---|---|
With ammonium hydroxide In water at 5 - 15℃; for 3h; pH=9; Inert atmosphere; Darkness; | 93% |
L-epinephrine
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol; water at 40℃; for 4h; | 89.7% |
L-epinephrine
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; ammonium formate In methanol at 50℃; | 86% |
L-epinephrine
Conditions | Yield |
---|---|
With formic acid; palladium 10% on activated carbon In methanol at 50℃; for 2h; | 81% |
L-epinephrine
Conditions | Yield |
---|---|
With formic acid; palladium 10% on activated carbon In methanol at 50℃; for 1h; | 74% |
R-(+)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-hydroxy-2-methylamido-ethan
L-epinephrine
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol for 6h; Ambient temperature; | 53.7% |
adrenalone
B
L-epinephrine
C
(S)-4-[1-hydroxy-2-(methylamino)ethyl]pyrocatechol
Conditions | Yield |
---|---|
With tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide; isopropyl alcohol Electrochemical reaction; Title compound not separated from byproducts.; | A 5% B n/a C n/a |
L-epinephrine
Conditions | Yield |
---|---|
With D-tartaric acid |
Conditions | Yield |
---|---|
With water; hydrogen; platinum aus der methylalkoholischen Loesung des Reaktionsprodukts scheidet sich das saure d-Tartrat des l-Adrenalins zuerst aus; |
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 1.) (-)-2-(2-HO-3-Br-5-t-Bu-C6H2-CH=N)-2'-HO-1,1'-binaphthyl, Ti(O-iPr)4, 2-HO-3,5-t-Bu2-C6H2-COOH, 2.) Me3SiCl, Et3N, 4.) TFA / 1.) toluene, 23 deg C, 1 h and 1 h, 23 deg C, 2.) toluene, -20 deg C, 15 min, 3.) toluene, -20 deg C to 23 deg C, 6 h, 4.) THF 2: imidazole / dimethylformamide 3: NaOH / H2O; methanol 4: SOCl2 5: NH4OH 6: 1.) PhI(OAc)2, KOH, 2.) LiAlH4 / 2.) THF, heating 7: 97 percent / BBr3 View Scheme |
A
L-epinephrine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) PhI(OAc)2, KOH, 2.) LiAlH4 / 2.) THF, heating 2: 97 percent / BBr3 View Scheme |
(S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(3,4-dimethoxy-phenyl)-propionic acid
A
L-epinephrine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: SOCl2 2: NH4OH 3: 1.) PhI(OAc)2, KOH, 2.) LiAlH4 / 2.) THF, heating 4: 97 percent / BBr3 View Scheme |
A
L-epinephrine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: NH4OH 2: 1.) PhI(OAc)2, KOH, 2.) LiAlH4 / 2.) THF, heating 3: 97 percent / BBr3 View Scheme |
(S)-3-(3,4-Dimethoxy-phenyl)-3-hydroxy-propionic acid benzyl ester
A
L-epinephrine
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: imidazole / dimethylformamide 2: NaOH / H2O; methanol 3: SOCl2 4: NH4OH 5: 1.) PhI(OAc)2, KOH, 2.) LiAlH4 / 2.) THF, heating 6: 97 percent / BBr3 View Scheme |
A
L-epinephrine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: NaOH / H2O; methanol 2: SOCl2 3: NH4OH 4: 1.) PhI(OAc)2, KOH, 2.) LiAlH4 / 2.) THF, heating 5: 97 percent / BBr3 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 73 percent / NaHCO3 / benzene; H2O / 30 h 2: NaBH4 / methanol / 24 h 3: 53.7 percent / H2, conc HCl / Pd/C / ethanol / 6 h / Ambient temperature View Scheme | |
Multi-step reaction with 3 steps 1: hydrogen; palladium(II) hydroxide / water; methanol / 16 h / 10 - 40 °C / 150.01 Torr 2: methanol / 20 h / 20 °C / Large scale 3: ammonium hydroxide / water / 3 h / 5 - 15 °C / pH 9 / Inert atmosphere; Darkness View Scheme |
R-(+)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-oxo-2-methylamido-ethan
L-epinephrine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaBH4 / methanol / 24 h 2: 53.7 percent / H2, conc HCl / Pd/C / ethanol / 6 h / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
Stage #1: L-Tartaric acid; Epinephrine at 20℃; for 1 - 3h; Stage #2: With ammonia; sodium hydrogensulfite In water at 5 - 10℃; for 0.25h; pH=8.5; Product distribution / selectivity; |
Conditions | Yield |
---|---|
With (R)-epinephrine dehydrogenase; NADH In aq. phosphate buffer at 45℃; pH=6; Kinetics; Reagent/catalyst; pH-value; Temperature; Enzymatic reaction; enantioselective reaction; | n/a |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: acetonitrile; water / 3 h / 0 - 40 °C / Large scale 1.2: 1.5 h / 5 - 25 °C / Large scale 2.1: hydrogen; palladium(II) hydroxide / water; methanol / 16 h / 10 - 40 °C / 150.01 Torr 3.1: methanol / 20 h / 20 °C / Large scale 4.1: ammonium hydroxide / water / 3 h / 5 - 15 °C / pH 9 / Inert atmosphere; Darkness View Scheme |
norepinephrine
S-Adenosyl-L-methionine
L-epinephrine
Conditions | Yield |
---|---|
With N-methyltransferase; 2-Amino-1-phenylethanol Enzymatic reaction; |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: tetrahydrobiopterin; oxygen; tyrosine hydroxylase / Enzymatic reaction 2: aromatic L-amino acid decarboxylase / Enzymatic reaction 3: oxygen; dopamine β-hydroxylase; ascorbic acid / Enzymatic reaction 4: 2-Amino-1-phenylethanol; N-methyltransferase / Enzymatic reaction View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: aromatic L-amino acid decarboxylase / Enzymatic reaction 2: oxygen; dopamine β-hydroxylase; ascorbic acid / Enzymatic reaction 3: 2-Amino-1-phenylethanol; N-methyltransferase / Enzymatic reaction View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: sodium carbonate / tetrahydrofuran; water / 5 h / 20 °C 2: trichlorophosphate / 3.5 h / 60 °C 3: water; ethanol / 2 h / 60 °C 4: sodium tetrahydroborate / ethanol / 5 h / 20 °C 5: hydrogenchloride / water; ethanol / 4 h / 40 °C View Scheme |
L-epinephrine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: trichlorophosphate / 3.5 h / 60 °C 2: water; ethanol / 2 h / 60 °C 3: sodium tetrahydroborate / ethanol / 5 h / 20 °C 4: hydrogenchloride / water; ethanol / 4 h / 40 °C View Scheme |
L-epinephrine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: water; ethanol / 2 h / 60 °C 2: sodium tetrahydroborate / ethanol / 5 h / 20 °C 3: hydrogenchloride / water; ethanol / 4 h / 40 °C View Scheme |
Epinephrine
A
L-epinephrine
B
(S)-4-[1-hydroxy-2-(methylamino)ethyl]pyrocatechol
Conditions | Yield |
---|---|
With core-shell macrocyclic glycopeptide-based chiral stationary phase NicoShell In methanol; acetic acid; acetonitrile at 20℃; Reagent/catalyst; Resolution of racemate; | |
With phase-transitioned bovine serum albumin film-coated capillary column In methanol pH=8.5; Resolution of racemate; |
Conditions | Yield |
---|---|
With pyridine; triethylamine In tetrahydrofuran at 40℃; for 3.5h; | 85% |
Conditions | Yield |
---|---|
With pyridine; triethylamine In tetrahydrofuran at 40℃; for 3.5h; | 84% |
Conditions | Yield |
---|---|
With pyridine; triethylamine In tetrahydrofuran at 40℃; for 4h; | 82% |
diethyl (α-acetoxymethyl)vinylphosphonate
L-epinephrine
(R)-diethyl 3-((2-(3,4-dihydroxyphenyl)-2-hydroxyethyl)methylamino)prop-1-en-2-ylphosphonate
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane In tetrahydrofuran at 20℃; for 24h; | 81% |
Conditions | Yield |
---|---|
With pyridine; triethylamine In tetrahydrofuran at 40℃; for 3h; | 81% |
Conditions | Yield |
---|---|
With pyridine; triethylamine In tetrahydrofuran at 40℃; for 3h; | 80% |
Conditions | Yield |
---|---|
With pyridine; triethylamine In tetrahydrofuran at 40℃; for 3.5h; | 79% |
Conditions | Yield |
---|---|
With pyridine; triethylamine In tetrahydrofuran at 40℃; for 4h; | 76% |
Conditions | Yield |
---|---|
In water for 8h; | 76% |
Conditions | Yield |
---|---|
With pyridine; triethylamine In tetrahydrofuran at 40℃; for 3h; | 75% |
Conditions | Yield |
---|---|
With pyridine; triethylamine In tetrahydrofuran at 40℃; for 2.5h; | 74% |
Conditions | Yield |
---|---|
With pyridine; triethylamine In tetrahydrofuran at 40℃; for 3h; | 73% |
L-epinephrine
3-chloro-4-fluorophenyl isothiocyanate
Conditions | Yield |
---|---|
With pyridine; triethylamine In tetrahydrofuran at 40℃; for 2.5h; | 72% |
2,6-difluorophenylisothiocyanate
L-epinephrine
Conditions | Yield |
---|---|
With pyridine; triethylamine In tetrahydrofuran at 40℃; for 3.5h; | 71% |
(R)-4-methyl-3-(3'-oxobutyl)pent-4-enal
L-epinephrine
Conditions | Yield |
---|---|
With trimethylamine-N-oxide; C27H28FeN3O3(1+)*BF4(1-); hydrogen In ethanol at 20℃; under 3750.38 Torr; for 16h; Autoclave; Inert atmosphere; chemoselective reaction; | 65% |
formaldehyd
L-epinephrine
1,2,3,4-tetrahydro-2-methyl-4,6,7-isoquinolinetriol hydrochloride
Conditions | Yield |
---|---|
In hydrogenchloride; water for 18h; Ambient temperature; | 57% |
With hydrogenchloride; sodium hydrogencarbonate In water at 20℃; for 18h; | 49% |
L-epinephrine
Conditions | Yield |
---|---|
In dimethyl sulfoxide; acetone | 48% |
L-epinephrine
(R)-[1'-amino-2'-hydroxy-2'-(4''-hydroxyphenyl)propionic acid methyl ester]-carbamic acid p-(bis-2-chloroethylamino)phenyl ester
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 20℃; for 72h; | 44% |
formaldehyd
L-epinephrine
A
1,2,3,4-tetrahydro-2-methyl-4,6,7-isoquinolinetriol hydrochloride
B
1,2,3,4-tetrahydro-2-methyl-4,7,8-isoquinolinetriol hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydrogencarbonate In water for 1h; | A n/a B 22% |
(+/-)-9-hydroxy-10-oxo-12(Z),15(Z)-octadecadienoic acid
L-epinephrine
A
C27H41NO8
B
C27H41NO8
Conditions | Yield |
---|---|
With oxygen; tris hydrochloride In water; dimethyl sulfoxide at 25℃; for 15h; pH=8.0; | A 18% B 8% |
With oxygen In water at 25℃; for 15h; pH=8; |
L-epinephrine
Conditions | Yield |
---|---|
In ethanol addn. of a soln. of metal salt in ethanol to a soln. of adrenaline in ethanol at 50°C with stirring; washing with ethanol, drying in vac.; elem. anal.; | 15% |
Conditions | Yield |
---|---|
With sodium methylate In methanol; butan-1-ol for 20h; Heating; | 5% |
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